Regioselective synthesis of o-triazolyl-1,5-benzodiazepin-2-ones and o-isoxazolyl-1,5-benzodiazepin-2-ones via copper-catalyzed 1,3-dipolar cycloaddition reactions

H. Mtiraoui , A. Nsira , M. Msaddek (1) , Pierre-Yves Renard (2) , Cyrille Sabot (2)

1 CHPNR - Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité [Monastir]
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

A series of novel O-triazolyl-1,5-benzodiazepin-2-ones 6a–o and O-isoxazolyl-1,5-benzodiazepin-2-ones 7a–o was synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne–azide coupling reaction of N-substituted-1,5-benzodiazepine–alkyne derivatives 3a–c with various aromatic azides 4a–e and nitrile oxides 5a–e, respectively. The chemical structures of synthesized compounds were determined using 1H NMR, 13C NMR, heteronuclear multiple bond correlation (HMBC), high-resolution mass spectra, as well as elemental analysis and was further confirmed by an X-ray diffraction analysis for compound 7d.

Mots clés: 3; 5-Disubstituted isoxazole; Terminal alkyne; 2; Click chemistry; 1; 5-Benzodiazepines; 3-Triazoles

Domaines: Chimie

H. Mtiraoui, A. Nsira, M. Msaddek, Pierre-Yves Renard, Cyrille Sabot. Regioselective synthesis of o-triazolyl-1,5-benzodiazepin-2-ones and o-isoxazolyl-1,5-benzodiazepin-2-ones via copper-catalyzed 1,3-dipolar cycloaddition reactions. Comptes Rendus. Chimie, 2017, 20 (7), pp.747-757. ⟨10.1016/j.crci.2017.02.004⟩. ⟨hal-02046301⟩